title: Synthesis and biological activity of thiazolyl-acetic acid derivatives as possible antimicrobial agents.
abstract: 5a-h, a series of (5-substituted-2-methyl-1,3-thiazole-4-yl) acetic acids as heterocyclic acetic acid derivatives, was designed and synthesized from ethyl acetoacetate. The synthesized compounds were screened for their antimicrobial activities against bacterial and fungal strains, and their characteristics were investigated by assays under various temperature and pH conditions. Cytotoxicity was evaluated with the use of sheep erythrocytes and human neonate dermal fibroblasts. Similarly, agents such as lauric acid 6 and parabens 7a-b, which are used as preservative agents for commercial cosmetics and detergents, were assayed for comparison. Although the structure of 5a is simple, comprising a thiazole attached with an octyl group and acetic acid moiety, the compound showed stronger and broader antibacterial and antifungal activities among the 5 series against the tested microbes other than gram-negative bacteria. Interestingly, 5a overcame the weak antifungal activity of parabens 7a-b. Also, the cytotoxicity of 5a was less than that of parabens 7a-b, especially to human dermal fibroblasts. These results suggest that thiazolyl-acetic acid 5a is a potentially effective biocide, and that it could be used as a preservative agent in commercially sold cosmetics and detergents, facilitated by the hydrophilic and charge properties of its carboxylic acid moiety.
authors.affiliation: Department of Biological Science and Technology, Biosystems Engineering, Institute of Technology and Science, The University of Tokushima, 2-1, Minamijosanjima-cho, Tokushima 770-8506, Japan. shirai@bio.tokushima-u.ac.jp
authors.forename: Akihiro
authors.initials: A
authors.lastname: Shirai
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Fumoto
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Shouno
authors.forename: Hideaki
authors.initials: H
authors.lastname: Maseda
authors.forename: Takeshi
authors.initials: T
authors.lastname: Omasa
mesh_terms: D019342:Acetic Acid / Q000737:chemistry / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D015195:Drug Design; D005658:Fungi / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D013844:Thiazoles; D019342:Acetic Acid